What Should’ve Won That Could’ve Won: 2012

The Year: 2012
What the Nominees Were: Amour, Argo, Beasts of the Southern Wild, Django Unchained, Life of Pi, Lincoln, Les Miserables, Silver Linings Playbook, Zero Dark Thirty
Other Movies That Should Have Been Considered: Paul Thomas Anderson’s The Master is a pretty master-ful. How on earth was it not even nominated??

What Did Win: Argo
How It’s Aged: It’s odd that people don’t cite this one more often as a great Oscar injustice. An entirely fictionalized “true story” with workman-like (not even nominated) direction—How did it win Picture? Hollywood just loves stories about Hollywood saving the day.

What Should’ve Won: Lincoln
How Hard Was the Decision: A very hard choice between Lincoln and The Master, because neither is a perfect film. Lincoln errs on the side of being too slick, pretty, and anodyne, while The Master errs on the side of being too bizarre, rough, and oddly paced. Rewatching Lincoln, I was once again offended by the ways Spielberg and Kushner have cleaned up Lincoln’s character to fit our modern version of liberalism. Lincoln genuinely thought most Black men should never be given the right to vote, but they try to gloss over that to make him an unambiguous hero. Goodwin’s fetishization of moderation (the book came out just as Obama took office and by all accounts had a big influence on him) is pernicious and leaks into the movie, which feels the need to throw Thaddeus Stevens, a much better person than Lincoln, under the bus to make Lincoln look better. So I’m torn about giving this movie an Oscar. But ultimately, The Master is just too odd, so I’ll reluctantly go with this one.

Director: Steven Spielberg
Writer: Tony Kushner, very loosely based on “Team of Rivals” by Doris Kearns Goodwin
Stars: Daniel Day-Lewis, Sally Field, David Strathairn, Joseph Gordon-Levitt, James Spader, Hal Holbrook, Tommy Lee Jones (plus about two dozen not-yet-famous-faces in bit parts like Adam Driver.)

The Story: In January 1865, Abraham Lincoln must wrap up the Civil War and get the 13th Amendment passed before the southern states rejoin.

Any Nominations or Wins: It only won Actor and Production Design. It lost Picture, Director, Supporting Actor for Jones, Supporting Actress for Field, Adapted Screenplay, Cinematography, Costume Design, Editing, Score and Sound Mixing. Whew, that was a long list!

Why It Didn’t Win: I truly have no idea. The Academy has always liked nominating Spielberg more than actually giving him awards (The Color Purple famously had eleven nominations and no wins) and these dangled carrots fit that bill. But to lose to Argo?? Pretty baffling.

Why It Should Have Won:

1. Spielberg only hired Day-Lewis because the timing didn’t work out with Liam Neeson and that’s a bullet past the ear if there ever was one! The movie takes liberties with the character, but Day-Lewis could not be more authentic, according to all the reports we have: from Lincoln’s high reedy voice to his ability to command a room without shouting, to his prematurely aged appearance, Day-Lewis is simply uncanny.
   
2. The lesson of Lincoln, and Lincoln, is that the greatest weapon a president can have is the ability to disarm (and thereby defang) his adversaries, which Lincoln does with an endless stream of inappropriate (but pointed) back-woods humor. (This is a weapon that LBJ and GWB also wielded expertly, for good or ill). Kushner and Day-Lewis masterfully recreate Lincoln’s canny charade: folksy hick on the surface, quick-eyed political mongoose underneath.
3. A good movie, even a biopic, isn’t about a person, it’s about a person’s problem. Kushner famously started out by attempting to cover 1863-65, but he got through hundreds of pages without making it to 1864, so he started over. Then he tried to just cover the four months of 1865, which turned out to be 500 pages! (Somebody publish that version please!) Spielberg, to his infinite credit, got to page 100 and said, “Hey, that’s a movie right there, let’s just stop at the end of January.” This isn’t really a bio-pic: it’s just the story of one problem: the passing of the 13th Amendment in the House. Of course, in Kushner’s capable hands, that’s enough to give a compelling portrait of the man with the plan.
   
4. Spielberg and Kushner know full well that, on a moral level, the audience is going to identify more with Stevens, but they also have to stress how radical he seemed to be at the time, and why Lincoln regarded him as more of liability than an asset in the fight against slavery. They get a lot of storytelling power out of that irony, ultimately leading up to the big reveal that Stevens has a secret Black common-law wife, which makes everything he said seem all the more ironic in retrospect.
   
5. (The problem with claiming this is based on Goodwin’s book, when it manifestly is not, is that there is a lot of great material in the book that will now never get adapted! The real star of the book is Salmon Chase, an enormously complex character who deserves his own movie, but he gets not even a mention here, alas.)
6. Kushner went through his finished script with a copy of the Old English Dictionary to make sure every word he used already existed in 1865, and indeed the language feels very authentic, with lots of great words like “flubdubs” and “pettifogging.” (When I wrote my Alan Turing biopic, I got dinged for using the word “newbie.”)

What Should’ve Won That Could’ve Won: 2011

The Year: 2011
What the Nominees Were: The Artist, The Descendants, Extremely Loud and Incredibly Close, The Help, Hugo, Midnight in Paris, Moneyball, The Tree of Life, War Horse
Other Movies That Should Have Been Considered: Bridesmaids is pretty great, as is Rise of the Planet of the Apes. Crazy Stupid Love is better than a lot of the nominees (Hugo?? Easily Scorsese’s worst film.)  Overseas, the Iranian movie A Separation was very powerful.  

What Did Win: The Artist
How It’s Aged: It’s still pretty adorable. A lovely little movie that would be totally forgotten if it hadn’t won Best Picture (and is still pretty forgotten at that.) Generally seen as one of the most undeserving wins, but if they had to pick one of those nominees, this one isn’t bad.

What Should’ve Won: Bridesmaids
How Hard Was the Decision: A very hard choice because A Separation didn’t seem like it could’ve won, so I was left with American movies, and there were no five-star American movies this year. Ultimately, this was the four-star movie I had the most affection for.

Director: Paul Feig
Writers: Annie Mumolo and Kristen Wiig
Stars: Kristen Wiig, Maya Rudolph, Rose Byrne, Wendi McLendon-Covey, Ellie Kemper, Melissa McCarthy, Chris O’Dowd

The Story: Annie Walker is a failed bakery-owner whose best friend Lillian is getting married to a man in another city. Annie is devastated, but agrees to be her maid of honor, only to find herself in competition with Lillian’s new friend, a brittle trophy wife named Helen. Annie’s whole life falls apart, but she attempts a new romance with a charming cop, and eventually makes friends with fellow bridesmaids Becca, Rita, and especially Megan, which gets her past her depression.

Any Nominations or Wins: It was nominated for Original Screenplay and Supporting Actress for McCarthy, but won neither
Why It Didn’t Win: I would say it was a long shot because it was a comedy, but it was beat by a comedy that was French and silent, so that can’t be it! Generally speaking, based on the number of shockingly weak nominations, the Academy had just lost their damn minds this year.

Why It Should Have Won:

1. Judd Apatow directed or produced a lot of comedies in this era, but this was the best of the bunch (and, surprisingly, the most profitable.) Feig and Apatow had worked together on the TV show “Freaks and Geeks”, and Feig proves the defter directorial touch of the two. Hilarious Apatovian moments such as the bodily-flued spewing dress-fitting scene are balanced out by moments of more genuine emotion.
   
2. We fall in love with Annie when she wakes up next to Jon Hamm, feels self-conscious, sneaks out of bed, does her hair and make up, then sneaks back into bed and pretends to wake up as he does. The character will be fairly downtrodden and hapless, but this one moment of clever resourcefulness is enough to convince us she will have what it takes to come out on top in the end.
   
3. Wiig and Rudolph were old “Saturday Night Live” castmates and develop a very convincing chemistry here as the sort of easygoing old friends that we all wish we had more of. When they put food in their teeth in the opening scene to crack each other up, we get the instant feeling that this is a real friendship, as indeed it was.
   
4. Robert Kirkman famously created “The Walking Dead” to explore what happens after most zombie movies end. Likewise, Bridesmaids shows what happens after most romantic comedies end. She’s already had the traditional happy ending: her boyfriend helped her start her own business doing what she loved to do! But what happens when the economy crashes, the bakery fails and the boyfriend leaves? (It always drives me nuts how many comedies end with “let’s start our own business,” as if that’s not usually a disastrous decision!) This movie does a great job dealing with the real life national pain of 2011.
5. It’s understandable that McCarthy got the only nomination from the cast, because she became the breakout star with her hilariously profane take on Megan. She would rise to the task of headlining her own movies based on the strength of this one, despite not looking like a traditional movie star.
   
   
   
   
   

What Should’ve Won That Could’ve Won: 2010

The Year: 2010
What the Nominees Were: The Black Swan, The Fighter, Inception, The Kids Are All Right, The King’s Speech, 127 Hours, The Social Network, Toy Story 3, True Grit, Winter’s Bone
Other Movies That Should Have Been Considered: That’s a good list, but How to Train Your Dragon is also pretty great.

What Did Win: The King’s Speech

How It’s Aged: When people complain about stuffy, talky, stiff-upper-lip Best Pictures, this one is frequently singled out for derision, but it’s a perfectly fine movie. Just not a Best Picture.

What Should’ve Won: The Fighter
How Hard Was the Decision: The Black Swan, True Grit and How to Train Your Dragon are all brilliant, but I love The Fighter even more.

Director: David O. Russell
Writers: Scott Silver, Paul Tamasy and Eric Johnson, from a story by Keith Dorrington, Tamasy and Johnson
Stars: Mark Wahlberg, Christian Bale, Amy Adams, Melissa Leo

The Story: The true story of welterweight boxer Mickey Ward from Lowell, Massachusetts, who foolishly puts his career in the hands of his crackhead older brother Dicky and short-sighted mother Alice. Only when Dicky goes to prison does Mickey, with the encouragement of a tough new girlfriend, decide to finally get serious about his career. But just when he gets his shot at the big time, Dicky gets out and insists on retaking control.

Any Nominations or Wins: It won Supporting Actor for Bale and Supporting Actress for Leo. It lost Picture, Director, Supporting Actress for Adams, Original Screenplay and Editing.
Why It Didn’t Win: Once again, we have the heavy hand of Harvey Weinstein to blame. Weinstein threw his then-still-considerable weight behind The King’s Speech and pushed it over the finish line, ahead of several more noteworthy contenders, including this one.

Why It Should Have Won:

1. Bale is one of our best actors and took home a well-deserved statue here, but Adams lost out to her co-star Leo, which is a shame because she’s great playing completely against type (she gets to throw some punches herself!) As of this writing, Adams has still never won, despite being one of the best actresses of her generation.
   
2. Ward is famous today for the three knock-down, drag-out title fights he fought against Arturo Gatti. But you won’t see those here. The writers took a good look at his life, decided that the best story was Ward’s struggle with his own family, and then ruthlessly pared that story down to its essence. We begin when Ward finally becomes aware of that problem and we end when that problem is ultimately resolved. The Gatti fights came about because Ward had solved his problems outside the ring, so they have no place here.
3. Crack addiction! Police brutality! Bloodsport! This could have been a very turgid drama. Instead, against all odds, it’s absolutely hilarious at least half the time. These people don’t know they’re in a drama. And it’s only because of the comedy that the drama works. We would give up on these people ten minutes in if they weren’t so endearingly goofy.
   
4. How many chances do the mother and brother get to ruin everything before they finally get it right? We get to the point where they’ve totally rubbed us raw. The hair goes up on the back of our neck whenever they enter the room. Then they finally surprise us. That’s how to create expectations before you defy them at the last possible minute.
5. We start off pitying these fools for giving the crackhead in the family too many chances, but soon we start loving him too and we’re right there with them rooting for him, against our own instincts. The movie humbles us with a simple Christian moral: Never give up on anyone, no matter what.

What Should’ve Won That Could’ve Won: 2009

The Year: 2009
What the Nominees Were: The number of nominations went back up to ten, where it’s remained ever since. Avatar, The Blind Side, District Nine, An Education, The Hurt Locker, Inglorious Basterds, Precious, A Serious Man, Up, Up in the Air

Other Movies That Should Have Been Considered: Steven Soderbergh’s The Informant! is excellent. In the Loop from England deserved a nomination.

What Did Win: The Hurt Locker
How It’s Aged: It’s great that a movie by a woman director finally won Best Picture, but it’s sort of a joke that Kathryn Bigelow only won by making an all-male testosterone fest. This movie questioned what we were actually doing in Iraq in so quiet of a voice, that it could easily be mistaken for a recruiting poster.

What Should’ve Won: An Education
How Hard Was the Decision: Not that hard because I love this movie. I thought it would be nice to give it to a different movie, also directed by a woman, that actually dared to give speaking roles to women!

Director: Lone Scherfig

Writer: Nick Hornby, based on the memoir by Lynn Barber

Stars: Carey Mulligan, Peter Sarsgaard, Alfred Molina, Rosamund Pike, Dominic Cooper, Olivia Williams, Emma Thompson

The Story: In 1961 London, Oxford-obsessed 16 year old Jenny Mellor loses her interest in going to college as she gets seduced by a conman, getting a different type of “education.” When she realizes that he’s already married, she has to get her life back on track.

Any Nominations or Wins: It lost Picture, Actress and Adapted Screenplay
Why It Didn’t Win: Hollywood couldn’t resist pitting Bigelow against James Cameron, the ex-husband who cheated on her, making Hurt Locker and Avatar the only two real contenders. An Education got nominated but got lost in the new sea of ten nominees and forgotten.

Why It Should Have Won:

1. In the commentary, Sarsgaard points out a brilliant thing Scherfig does. In one scene, the whole point is that Jenny’s mom fails to speak up about the danger Jenny is putting herself in, so Scherfig subconsciously calls attention to that: “There’s an expectation created by the camera move that comes up later that the mother’s going to say one last thing, but she doesn’t. Like right here, in cinema language, she supposed to say one last thing right there.” A brilliant way to subtly dramatize something not happening.
   
2. The original memoir (really just a magazine piece) is well worth reading. There are so many things here that only could have come from real life because no one would make them up. Real sex is always so much weirder than movie sex, as shown here when David bizarrely wants to deflower Jenny with a banana.
3. I love how Hornby’s dialogue avoids the Sorkin Stammer. Jenny thinks highly of her own verbal abilities, and frequently tries to skewer whomever she’s talking to. In some scripts, her victims would just stammer helplessly because they had met a superior wit, but in this script, ever single person our hero tries to skewer whaps her right back (or at least has the wherewithal to say some version of, “It sucks that you’re talking to me that way.”) My favorite exchange: Jenny says to her headmistress, Emma Thompson, “I suppose you think I’m a ‘fallen woman.’” To which Thompson bats back, “Oh, you’re not a woman.”
   
4. Most deleted scenes are ultimately inconsequential, but here we have one that could not have been more important: Jenny’s only real confrontation with David after the truth comes out! But it was brilliant to cut it. The scene had way too much closure. What’s so great about the final onscreen ending is that it’s haunting. She never expunges the ghost of David, so he hovers over her whole life. She can pretend that it never happened, but she’ll always know better. Scherfig knew she had a brilliant script on her hands...but she also knew that the last page blew it, and a better one would make it a classic. She kept pushing until she found the bittersweet ending the movie needed. (Sarsgaard says the confrontation scene “never felt right in any way, shape or form.”)
5. Everything in this movie just swings. The clothes David buys her, the locations he takes her to, and especially the music playing there are delightfully hip. Who knew Mel Tormé could rock out? The country was waiting for the Beatles to wake them up (Jenny says “This whole stupid country is bored”) but, in some ways, it never looked cooler.
   
6. One thing I love about the movie is how low-stakes it is. Nobody ever pulls a gun. It’s just one girl’s education on the line, which is a hard way to make a movie, but refreshing. Sherfig says in the doc: “I was always taught that it doesn’t matter if a little girl’s dress is torn, or if 500 soldiers get killed on film, it’s a matter of which scale you weigh things on, and this film is hopefully as emotional as if something much more drastic had happened.”

What Should’ve Won That Could’ve Won: 2008

The Year: 2008

What the Nominees Were: The Curious Case of Benjamin Button, Frost Nixon, Milk, The Reader, Slumdog Millionaire
Other Movies That Should Have Been Considered: How did The Wrestler and Doubt not get nominations?? They’re certainly both better than Frost Nixon (which is an okay movie, but still!)

What Did Win: Slumdog Millionaire
How It’s Aged: It certainly has dated cinematography and editing. Very melodramatic story driven by a series of huge coincidences (every single question on “Who Wants to Be a Millionaire?” can be answered by a trauma from his past?) And why would the host be rooting against him? Winners are big ratings. I didn’t get this movie.

What Should’ve Won: Milk
How Hard Was the Decision: A very hard choice between Milk, The Wrestler and Doubt. Three fantastic films, but this inspiring biopic felt the most like an Oscar winner to me.

Director: Gus Van Sant
Writer: Dustin Lance Black
Stars: Sean Penn, Emile Hirsch, Josh Brolin, Diego Luna, James Franco

The Story: Closeted New York office worker Harvey Milk turns 40 without having accomplished anything, so he gets a boyfriend, moves to San Francisco, opens a camera store, and starts running for office over and over until he finally gets a position on the Board of Supervisors. He and the mayor are assassinated by a fellow supervisor, who serves all of five years time for it.

Any Nominations or Wins: It won Actor and Original Screenplay. It lost Picture, Director, Supporting Actor for Brolin, Costume Design, Editing, and Score.
Why It Didn’t Win: Out of these five nominees it was a pretty baffling loss. One suspects that this was another Brokeback Mountain situation.

Why It Should Have Won:

1. The (non-Oscar) success of a movie like Brokeback Mountain is great, but it always opens up a can of worms, because it becomes a danger of the “lone example.” This is our turn in the spotlight? Is that how you see us? Do we always have to be closeted? Why can’t we be out and proud? This movie became a necessary corrective, showing the other half of the story. (Of course, another question was “Do we always have to get killed by homophobes?” and this movie was very much not a corrective to that, but it’s the nature of this story.)
2. I kept tearing up during the movie, not because of Harvey’s death but because of his speeches (stirringly scored by Danny Elfman) and the phone calls he gets from suicidal teenagers. This is an excellent old-fashioned good vs. evil movie, just with a different “good” than we normally get.
   
3. None of the major cast is gay, and there’s been a cultural shift in the years since that gay characters should be played by gay actors (though still not that Jewish actors should play Jewish characters, interestingly) but it’s hard to imagine anyone finding fault with Penn’s performance. The movie is heavily indebted to the documentary The Times of Harvey Milk, and with a wealth of footage of the real Harvey, Penn was able to channel Milk to an uncanny degree. (Gone are the days of Six Degrees of Separation when Will Smith could play a gay lead and yet refuse to kiss any guys, thankfully!)
   
4. Van Sant had made a series of excellent gay movies way outside the system and poised himself to be the one to get the call up when Hollywood was finally ready to tell this story. He keeps some of the independent spirit by cutting back and forth liberally between film stocks and interspersing lively tricks like this visualization of a phone tree. The movie pulses with life.
   
5. Early on, Harvey gets a death threat in the mail and puts it on his fridge to show he’s not afraid. Later, as threats increase, he finally becomes scared of it, takes it off and throws it away. A great use of showing internal change through objects.
   

What Should’ve Won That Could’ve Won: 2007

The Year: 2007
What the Nominees Were: Juno, Michael Clayton, No Country for Old Men, Atonement, There Will Be Blood
Other Movies That Should Have Been Considered: Nope, that’s a great list.

What Did Win: No Country for Old Men
How It’s Aged: It’s brilliant, one of the best movies of the 21st century. Certainly one of the most chilling villains ever presented. And yet…

What Should’ve Won: There Will Be Blood
How Hard Was the Decision: Extremely hard. How could I take away such a deserving Oscar win? But There Will Be Blood is even better. If I could move either of these by a year either way, they would both easily win.

Director: Paul Thomas Anderson
Writer: Anderson, very loosely based on the novel “Oil!” by Upton Sinclair
Stars: Daniel Day-Lewis and Paul Dano

The Story: In 1898 silver prospector Daniel Plainview discovers oil instead and shifts focus. When his shady practices kill one of his men, he adopts the man’s toddler son, H.W. Later H.W. is deafened in another accident, and his relationship with his father becomes more and more strained. Meanwhile, Daniel gets into an longstanding struggle with a preacher named Eli Sunday, resulting in a death-by-bowing-pin.

Any Nominations or Wins: It won Actor and Cinematography, but lost Picture, Director, Adapted Screenplay, Art Direction, Editing and Sound Editing.
Why It Didn’t Win: The Academy had unwisely passed over Fargo and now the Coens were overdue, so this movie just couldn’t compete with No Country for Old Men.

Why It Should Have Won:

1. Anyone whose read “The Jungle” won’t be surprised to hear that, in Sinclair’s novel, the anti-drilling heroes turn to socialism, but Anderson eliminates all that here (as well as all reference to the real-life Teapot Dome scandal). Instead, Anderson crafts a story similar in feel to that of a different muckraking novelist, Frank Norris, whose “McTeague” became the legendary silent movie Greed. Ultimately, Anderson was right to make the story his own. No one in the movie has the moral standing to heroically denounce Daniel, but the viewer sees enough to do that ourselves.
2. Usually, when I walk out of movie talking about its intrusive score, it’s because I didn’t like it (I’m looking at you, Hans Zimmer). This is one of the rare movies where the score is very noticeable and I actually loved it. Radiohead’s Johnny Greenwood makes the whole movie weirder and more discordant than it would have been, which is all to the good. (Anderson gives Greenwood a great showcase by having no dialogue in the first 15 minutes, which have a similar feel to a previous winner of mine, 2001: A Space Odyssey.)
   
3. Noted Hollywood asshole Quentin Tarantino recently picked a fight with this movie for no reason, claiming that it was ruined by a bad performance from Dano. I have no idea what he’s talking about. Dano is brilliant. Yes, it’s hard to compete when you have every scene opposite a never-better Day-Lewis, but Dano’s counterforce keeps those scenes crackling with life.
   
4. Wikipedia takes Daniel at his word when he says that he only adopted H.W. to make himself more appealing when he showed up to buy people’s land, but I don’t believe it. Daniel spends the whole movie looking for family, and it’s only when H.W. rejects him for the last time that Daniel lashes out with that claim. Yes, Daniel is an utterly evil psychopath, but that doesn’t mean that he doesn’t desire love and belonging as much as the next man, though he’s incapable of receiving it.
5. My favorite line from the movie is when Eli asks Daniel for money at the end and then adds “plus the five that is owed to me, with interest.” In the war of humiliations that has escalated between the men, Daniel had previously been “forced” to make a five thousand dollar donation to Eli’s church, but of course, it turns out he never paid it, because we all know that the secret of getting rich in America is to never pay your debts. And you scarcely even need to bury to succession of dead bodies you leave behind. No Country for Old Men may be an equally good movie to this one, and it’s got a great villain, but I find Daniel even more compelling, and I think he speaks to our real life national pain better, so I’ll give it to this one.
   

What Should’ve Won That Could’ve Won: 2006

The Year: 2006
What the Nominees Were: Babel, The Departed, Letters from Iwo Jima, Little Miss Sunshine, The Queen
Other Movies That Should Have Been Considered: Ryan Fleck and Anna Boden’s Half Nelson was pretty brilliant. Over in Germany, The Lives of Others was great.

What Should’ve Won and Did Win: The Departed
How Hard Was the Decision: Very hard, because The Departed is not an all-time classic. I slightly prefer Half Nelson and Letters from Iwo Jima, but not strongly enough that I felt like I could take away Scorsese’s win. In the end, possession is nine tenths of the law.

Director: Martin Scorsese
Writer: William Monahan, based on the movie Infernal Affairs, screenplay by Alan Mak and Felix Chong
Stars: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, Alec Baldwin

The Story: Conflicted cop Billy Costigan goes deep undercover infiltrating the operation of Boston mob boss Frank Costello, but Costello has his own infiltrator in the police, a go-getter named Colin Sullivan. Which rat will sniff out the other first, and will anyone be left alive?

Any Other Nominations or Wins: It won Picture, Director, Adapted Screenplay and Editing. It lost Supporting Actor for Wahlberg.
How It Won: I remember that it was a little shocking at the time, because reviews were not ecstatic, but Scorsese had never won and it was time to make up for past slights. Scorsese is one of the most beloved figures in Hollywood, and this movie was just good enough to get him across the finish line.

Why It Won:

1. This is not Scorsese’s best movie (I’ve already given one to Goodfellas, and Taxi Driver and Raging Bull are certainly better than this one, but got passed over in stronger years) but it is the most fun. It’s simply a thrilling cops-n-robbers shoot-em-up. It seems like everybody had a blast making it.
2. DiCaprio seems to have taken to heart the criticism of his terrible performance as an Irish-American in Scorsese’s earlier picture Gangs of New York and portrays the nationality much more authentically here. He talks on the DVD about the research he had to do. Damon and Wahlberg, on the other hand, are actually Southie guys and get to let that all hang out for once. Wahlberg got his only Oscar nomination and earns it, but Damon should have gotten one, too. Wahlberg says it was easy to channel the role from his childhood memories, with the only difference was that he was playing the kind of guy who used to arrest kids like him.
   
3. Costigan is ordered to put his info into an envelope, but the envelope has the word Citizen misspelled so he crosses it off and writes it correctly. Well, as it turns out, this envelope changes hands many times, and it’s very important that we notice it each time we see it, and characters who spot it briefly have to recognize it instantly. Crossing out that word was a brilliant way to do that.
   
4. Costello is closely based on real life criminal Whitey Bulger, who ran crime in Boston for 20 years while secretly informing for the FBI. Amazingly, Bulger was at large when they made this (#2 on the FBI’s Most Wanted list) which makes this a rather courageous story to tell. (Bulger was eventually caught, convicted and murdered in prison in 2018.)
5. There’s a lot of cultural appropriation going on here. Screenwriters Mak and Chong wrote a movie about their native Hong Kong, then Monohan kept just the bones of that and built a new story about his native Boston Irish, and Scorsese chose to direct it because it reminded him of growing up around the Italian-American mafia in Little Italy. For this movie to come together, everybody had to trust that what they knew was universal enough to fit into someone else’s framework.
6. There are X’s in every scene where somebody gets killed, which is a direct reference to the original version of Scarface, which did the same thing. Scorsese talks about in the extras how he couldn’t deal with the mob in the streets growing up because his asthma left him too weak to fight back, so he hid in the movie houses. The two places were equally important in giving Scorsese the abilities he would someday need.
   
7. Before this movie, screenwriters were terrified of cell phones. It seemed like these magical devices would make storytelling suddenly impossible, because they could solve most problems the writers could dream up. But this movie came up with all sorts of ways that cell phones, and the primitive state of texting, could create more dramatic possibilities, not fewer. (Of course, at the time, when phones still had keypads, you could text with your phone in your pocket, something you can’t do with modern phones.)